Sodium Azide → HCID 57517458, compound

Participants

Reaction Steps

To a stirred solution of crude diethyl 1-(3-bromopropyl)-1H-pyrrole-2,4-dicarboxylate in DMF (30 mL) was added sodium azide (1 g, 15.4 mmol). The resulting mixture was stirred at rt overnight then diluted with water (30 mL) and EtOAc (150 mL). After separation, the aqueous layer was extracted with EtOAc (2×150 mL). The combined organic layers were washed with brine, dried (MgSO4), and concentrated. Purification via flash chromatography (petroleum ether:EtOAc, 20:1 to 15:1) afforded diethyl 1-(3-azidopropyl)-1H-pyrrole-2,4-dicarboxylate (2 g, 75%). 1H NMR (CDCl3, 300 MHz) δ7.42 (s, 1H), 7.36 (s, 1 H), 4.40 (t, J=6.6 Hz, 2 H), 4.26 (m, 4 H), 3.30 (m, J=6.2 Hz, 2 H), 2.04 (m, 2 H), 1.36 (m, 6 H).

Provenance & Evidence